Paul Newman mastered the chambray work shirt more than 40 years ago—and he did it while working in a prison camp. Now that chambray has fully invaded, learn how to wear it by watching an originator

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Thanks to Cool Hand Luke, the 1967 drama about a defiant man stuck on Florida prison camp, Paul Newman—simultaneously embodying swaggering cool and sneering arrogance—burned an image of the perfectly dirty chambray work shirt into our brains. Even more impressive is how he paired it with a denim chore coat and never teetered—not even for a moment—into Canadian tuxedo territory. These days you're likely to trip over a dozen chambray shirts walking down Broadway, so to nail the Cool Hand Luke look and stand out from the chain gang, use this guide to wear it like so.